Cheap Flights to South Side from $33
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How Much Does it Cost To Fly To South Side?
The cheapest prices found with in the last 7 days for return flights were $56 and $33 for one-way flights to South Side for the period specified. Prices and availability are subject to change. Additional terms apply
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 10 hours ago
$56
Roundtrip
found 10 hours ago
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ATL | Chicago | June 2 to June 16 | $70 |
| ATL | Chicago | May 27 to May 28 | $86 |
| MSP | Chicago | June 9 to June 16 | $140 |
| MSP | Chicago | June 3 to June 10 | $140 |
| PHX | Chicago | May 19 to May 20 | $174 |
| MSP | Rockford | May 25 to May 27 | $186 |
| LAX | Chicago | May 28 to June 3 | $191 |
| ATL | Rockford | May 27 to May 29 | $196 |
| MCO | Rockford | May 27 to May 29 | $197 |
| DEN | Rockford | June 3 to June 9 | $205 |
| LAX | Chicago | May 11 to May 13 | $210 |
| PHX | Chicago | June 9 to July 21 | $215 |
| PHX | Rockford | June 16 to June 30 | $260 |
| MSY | Rockford | May 26 to May 28 | $322 |
| FCO | Chicago | May 20 to June 3 | $645 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| LAX | Chicago | May 9 to May 23 | $225 |
| ATL | Chicago | May 9 to May 16 | $228 |
| PHX | Chicago | May 9 to May 11 | $247 |
| DEN | Chicago | May 9 to May 10 | $250 |
| MSP | Chicago | May 10 to May 17 | $290 |
| MSY | Chicago | May 9 to May 12 | $331 |
| MCO | Chicago | May 9 to May 12 | $349 |
| IAH | Rockford | May 9 to May 11 | $363 |
| PHX | Chicago | May 9 to May 11 | $371 |
| ATL | Rockford | May 9 to May 11 | $389 |
| DEN | Rockford | May 8 to May 12 | $398 |
| MCO | Rockford | May 8 to May 11 | $497 |
| MSP | Rockford | May 8 to May 10 | $552 |
| LAX | Rockford | May 8 to May 11 | $579 |
| FCO | Chicago | May 10 to May 25 | $646 |
South Side Flight Information
Traveling to | South Side |
|---|---|
Lowest Price | $56 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Amazing South Side Accommodation Deals
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
$135 nightly
The price is $158 total per night from May 4 to May 5
$158 total
May 4 - May 5
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...
5.6/10 (1,001 reviews)
No elevator should be in bold. I had a bike with me and the narrow stairs were tough. Room's carpet looked like my friends rugby house floor after 3 years of not vacuuming and partying. Front desk saw me with a bike and still gave me a top floor room. Lady wandering the hotel knocking on all the ...
Reviewed on Apr 29, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$117 nightly
The price is $139 total per night from May 10 to May 11
$139 total
May 10 - May 11
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,211 reviews)
Honestly, for the price I thought a continental breakfast would have been nice. A microwave in the room? Hot tea? The only amenity they really bragged about was free wifi and that was down the entire weekend. That being said, beautiful hotel and great location! We enjoyed our stay very much!
Reviewed on May 1, 2026
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$116 nightly
The price is $138 total per night from May 25 to May 26
$138 total
May 25 - May 26
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (2,686 reviews)
I loved how it was near everything , no car needed , and how convenient in the same hotel you can get snacks and drinks 24 hours. If your from New York you know we are used to having bodegas open 24 hours so not even having to step out of the hotel to get your snacks and drinks 10 out of 10 and soo ...
Reviewed on May 2, 2026
Save an average of 15% on thousands of hotels when you're signed in
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$189 nightly
The price is $224 total per night from May 24 to May 25
$224 total
May 24 - May 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,067 reviews)
Lovely stay
Reviewed on Apr 23, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Luxury Hotels in South Side
The Wheeler Mansion
2020 South Calumet Avenue Chicago IL
$620 nightly
The price is $724 total per night from May 6 to May 7
$724 total
May 6 - May 7
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Soldier Field and Grant Park are located ...
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$116 nightly
The price is $138 total per night from May 25 to May 26
$138 total
May 25 - May 26
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (2,686 reviews)
I loved how it was near everything , no car needed , and how convenient in the same hotel you can get snacks and drinks 24 hours. If your from New York you know we are used to having bodegas open 24 hours so not even having to step out of the hotel to get your snacks and drinks 10 out of 10 and soo ...
Reviewed on May 2, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$189 nightly
The price is $224 total per night from May 24 to May 25
$224 total
May 24 - May 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,067 reviews)
Lovely stay
Reviewed on Apr 23, 2026
Save an average of 15% on thousands of hotels when you're signed in
Chinatown Hotel Chicago
214 West 22nd Place Chicago IL
$135 nightly
The price is $158 total per night from May 4 to May 5
$158 total
May 4 - May 5
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Popular attractions Soldier Field and Grant Park are located ...
5.6/10 (1,001 reviews)
No elevator should be in bold. I had a bike with me and the narrow stairs were tough. Room's carpet looked like my friends rugby house floor after 3 years of not vacuuming and partying. Front desk saw me with a bike and still gave me a top floor room. Lady wandering the hotel knocking on all the ...
Reviewed on Apr 29, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Family Friendly Hotels in South Side
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$189 nightly
The price is $224 total per night from May 24 to May 25
$224 total
May 24 - May 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,067 reviews)
Lovely stay
Reviewed on Apr 23, 2026
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
$116 nightly
The price is $138 total per night from May 25 to May 26
$138 total
May 25 - May 26
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (2,686 reviews)
I loved how it was near everything , no car needed , and how convenient in the same hotel you can get snacks and drinks 24 hours. If your from New York you know we are used to having bodegas open 24 hours so not even having to step out of the hotel to get your snacks and drinks 10 out of 10 and soo ...
Reviewed on May 2, 2026
Jaslin Hotel
261 West Cermak Rd Chicago IL
$117 nightly
The price is $139 total per night from May 10 to May 11
$139 total
May 10 - May 11
Total with taxes and fees
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,211 reviews)
Honestly, for the price I thought a continental breakfast would have been nice. A microwave in the room? Hot tea? The only amenity they really bragged about was free wifi and that was down the entire weekend. That being said, beautiful hotel and great location! We enjoyed our stay very much!
Reviewed on May 1, 2026
Save an average of 15% on thousands of hotels when you're signed in
Marriott Marquis Chicago
2121 South Prairie Avenue Chicago IL
$272 nightly
The price is $323 total per night from May 22 to May 23
$323 total
May 22 - May 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 9 restaurants, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Best South Side Flight and Hotel Packages
South Side flight + hotel packages - economy flights
Price found within the past 48 hours. Click for updated prices.
South Side flight + hotel packages - premium economy flights
Price found within the past 48 hours. Click for updated prices.
South Side flight + hotel packages - first class flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
Schiller Park, Illinois, USA
$20
$78 total
found 1 day ago
Midsize
Schiller Park, Illinois, USA
$21
$80 total
found 1 day ago
Standard
Schiller Park, Illinois, USA
$22
$82 total
found 1 day ago
Compact SUV
Schiller Park, Illinois, USA
$25
$89 total
found 1 day ago
Frequently asked questions
Plane Tickets To South Side
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to South Side. Browse through our inventory to explore a wide range of cheap flights to South Side to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in South Side as you anxiously await to exit the plane and explore what South Side has to offer. Considering all the amazing local food and culture in South Side, we won't hold this against you.
When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to South Side to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to South Side without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to South Side with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to South Side today!
More Ways To Wander
South Side Hotels
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South Side Vacation Rentals
Great Deals on alternative accommodations
South Side Car Rentals
Affordable cars to get you around town
South Side Vacations
Save more by combining flights, hotels and cars
Things to do in South Side
Activities, attractions and tours